Dress to Undress: Man Styles to Get You Laid (Maybe)

This is not my friend Tyler. If it was, he wouldn't need my help attracting women. That wiener dog/kissy face combo would do the trick.

In the following exchange, my friend Tyler, who often lets me pick his brain and publish the results, comes to me for advice on how to meet women. I don’t think Tyler needs help attracting women, he is an attractive dude, but he came to me for help. Like most intelligent people, he knows how to get what he wants: through flattery. Read as I dub his brand-new style “Hipster Clean” and send him off on his merry way to charm the pants off some poor unsuspecting Southern belle. Oh, and note that halfway through this conversation Tyler comes to the conclusion I am basically dressing him like my boyfriend. Also please excuse the fact that this was an online conversation, thus some online lingo, bad punctuation and Tyler’s ridiculous exclamatories, like “fuggin.” Please note that these are MY opinions, and I am dressing him like someone I would want to have sex with. So feel free to argue them in the comment section.

Tyler: So zoe, you’re all hip (SEE. FLATTERY.). i need some advice on how to be hip like you. you know.

Z: Is this in reference to you wanting to start a blog? I think you’re pretty hip.

Well kinda. I’m starting the blog this week, but I wanted your opinion on what you like your men to look like. I have no conception of what women really like, and I feel like i’m dressing like an old man.

Oh! Okay. Men should look put together but not like they tried to be put together. I also am a big fan of men in glasses, and with nice shoes. Oh, and no more hoodies in public.

No hoodies in public?

No more. It reminds me of high school.

That sucks. I fuggin’ love hoodies

Well I guess it depends. if you’re goin out..don’t wear a hoodie. Grocery store and gym, fine.

No! this has to be cut and dry. Like the ten commandments. I just don’t know where to begin. I don’t want to look preppy, but I don’t wanna look like I smoke Newports and drink PBR either

Okay then no more hoodies anywhere you think you might meet a lady. Gross Newports, that reminds me of the 7th grade. Okay so not a total hipster or yuppie.

Yeah like in-between.

Hipster Clean

I like that. There you go. Hipster Clean.

Well what do you wear now?

Jeans, high top Nikes and t-shirts. Sometimes a button down plaid something when I go out.

I like men in button ups. I also like men in sweaters but not gross sweaters. Mostly I like men in sweaters because I know I will steal them after we have sex.

That’s an interesting reason to like sweaters….quoted.

Haha. “That sweater looks soft…soon it shall be MINE”

You must have a lot of sweaters…

Hey, watch it! All the man sweaters I have come from the same small handful of men…(AS IF I NEED TO DEFEND MY SWEATER COLLECTION.)

Hah. What about a proper cut of jeans. Apparently girls like a slight hint of junk in the front. Which surprised me.

It’s not the junk, it’s the butt…But there is a fine line…too tight and it’s all wrong and you look like you’re a DJ in Williamsburg. But too baggy and you look all skinny and ick.


I looked at this photo and went MMMM. That’s the reaction you want.

Goood to know. I will try to find some mmm jeans.

It is good to have a pair of plain dark jeans to go out in.

I think my jeans might be a bit tight. two options: run or get different jeans. Running is cheaper.

Haha. Get ONE new pair of jeans and then run until your old ones fit. Oh wait! More important: boxers or briefs!?!

I do boxer briefs. Is that bad? SHOULD I WEAR BOXERS?

Haha no it was a trick question. The answer is always boxer briefs!

AWWW yea, my underwear is hip.

Do you have a nice pair of shoes?!

Yeah man, I love shoes. I wear Nike high tops.

Those are sneakers. I am talking SHOES.

OH geez, like what? Like loafers or something?

Here are some man shoe styles I want on my floor:

Shit those are slick shoes! Wait…on your floor?

Yes. On my floor. Along with the rest of their clothing.

OH. Does your boyfriend dress similarly to this?

Now that you mention it…yes…he has more shoes than I do. Well that is probably not true but he has a good baker’s dozen.

Omgwtf. Well I need to increase my standards in women. Thusly I need to increase my standards in my clothing.

Well he also wears tight jeans and has a mohawk that flops down all free-willy-in-captivity style. He is all hipster, and no clean. So…not what you’re goin for.

Ah interesting, didn’t think you’d date a dude with a mohawk.

I don’t care how he wears his hair. I like him to wear it how he likes it.

I suppose that is nice.

What kinda jacket you wearing?

None atm. I just wear regular jackets really… mostly hoodies. Spare me the lightning.

What is a “regular” jacket?

Oh shit, I don’t know.

No, I get it hoodies are mad comfy. I just stopped wearing them myself. Now if I want to be comfy I wear one of the aforementioned stolen man sweaters. Once, B (Editor’s note: My ex, who is also Tyler’s childhood best-friend) shrank all 8 of his sweaters at one time. I was given all of them! It was a glorious victory for my inner sweater hound.

I do the same thing with hats. I steal hats from girls.  I don’t wear them, I just steal them.

Why do u steal them?

….so they always have to call me back. Just kidding, it just sorta happens. I don’t actually steal them, just end up left at my place or in my car or something.

I remember you wearing a pea coat.

Yes, I do wear pea coats. Good or bad?

Good. But only in winter. Here, this jacket says I am stylish, not gay:

But it is kinda tight. Maybe don’t go that tight

Shit, that’s a nice jacket. I really like that.

Hey wow I feel good at this.

I knew it was a good idea to ask you.

My boyfriend also has a jacket like this, which confuses me, but does still make me want to undress him:

Hair suggestions?

Hair is the same rule of thumb. Make it look good but not like you spent time making it look good.

Hmm okay. So girls don’t like obvious prissiness, just the more subtle kind of it.

Yes. Well..no. We don’t like any prissiness. We want you to look roll out of bed sexy. But most people don’t ACTUALLY roll out of bed sexy.

Holy shit, sounds like your expectations are as high as men’s are.



Personally, I hate hair product.


I want to touch a man’s hair and have it not be flakey and hard. So if you’re using product make sure it doesn’t crust up.

Pomade. Gives the hold, but retains natural feel.

There you go.

boo yeah

Okay….flash forward six weeks and I get this little gem in my Facebook inbox:

With your advice on clothing, i got a new outfit, and got laid. Thank you.

Okay so who wants to argue with me on how men should dress? Boxers or briefs? Hair product? Hoodies?! Men, how do you dress to impress? 


About SexyTofu

Good food. Good sex. Good fun.
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13 Responses to Dress to Undress: Man Styles to Get You Laid (Maybe)

  1. asianbadass says:

    Great post! I definitely love your taste in clothes! The thing about hipster chic is that it thrives on a specific body type which is usually skinny and tall. I’m more of a short and muscle-bound type myself. So the types of clothing that I tend to go for accentuate broad shoulders and chest, and cinch a bit tighter in the waist. I stay away from things that run long n the torso because it makes me look shorter than I am. I love a good pair of nice shoes because you ladies NOTICE a nice pair of shoes. I’ll sometimes wear mens lifts, if I’m feeling saucy. It makes a good first impression, and my dates a little less self conscious.
    I agree on boxer briefs, though if I were doing casual, it’s usually boxers. On the style aspects though, I completely agree on everything you said! Great advice!

    • SexyTofu says:

      I’m really glad you said “If I’m feeling saucy.” I am glad men feel saucy. I like a guy in boxer briefs because boxers remind me of high school and well, plain briefs remind me of old men AND little boys at the same time. Obviously not gonna hold it against someone if they wear boxers or briefs, but neither will make me bite my bottom lip like a good pair of boxer briefs.

      • asianbadass says:

        Haha. Well I don’t know if all men feel saucy…I just know that I do on occasion. If I know I’m going to see a woman I’m interested in (or going somewhere where that’s a possibility) than boxer briefs are a must. They give the correct accent for a man. I agree on briefs…not a good look. Boxers for me are if I’m heading for the gym or if I’m at work (which is most of the time).

      • SexyTofu says:

        That’s totally understandable! Any man who has lived with a woman before knows she isn’t consistently wearing her lacies…

      • asianbadass says:

        It’s true! Sometimes she steals our boxers!

  2. What a great piece. You should try to sell it. I agree with everything. Hoodies always make me think of hold ups in convenient stores. In every Law and Order the robber always has one on. Good advice.

  3. Your friend Tyler sounds like a major cutie. Okay, so good call staying away from the hoodies. I scared my sleeping dog with my loud cackles after I read that they remind you of high school.

    Tyler, and all young men, should all continue the button down (plaid or not) shirts. I love that. Maybe just tuck in the front side and let the other loose, if that makes sense. Adds swagger, but it still looks a little Hipster. Nike hightops are fresh, love that. I also love a guy in Converse… old school and sexy with any pant…

    Oh yes, pants, jeans… ass is important but I’m one of those awkward crotch starers. A little junk in the front is so nice to see.

    Hair doesn’t matter much unless you’re rocking a ‘shroom cut circa 1995. If you don’t wear glasses, I say invest in the fake ones and wear them every now and then.

    Mmmm, men.

    • SexyTofu says:

      Hahaha shroom cut! The ones that your mom did by placing a bowl on your head. Or what about the awk front-flip from 2000? Sorta looks like the dude ran into a wall… oh if I EVER found out a dude wore fake glasses I would sexile him forever. Glasses are sexy but…pretend glasses? I secretly wish my eyes would be shittier so I could get some awesome huge glasses. But I know that I don’t really wish that because glasses are expensive…

  4. I agree–boxer-briefs! Other than that, hmm, I’m so out of it fashionably speaking, and I meet most guys at the gym, but in general I doubt, “beat up gym shorts and a sweaty t” is the answer…

    • SexyTofu says:

      I HATE when guys try to talk to me at the gym. Even when I was single, and even if they were attractive, it made me mad…I would be all CANT YOU SEE I AM SWEATING LIKE A FARM ANIMAL? Also if it didn’t work out, you have to see them all the time. Good for you for being able to deal with that, you’re more woman than I am.

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